The Yale-Vassar bike race found its origins in a drunken wager. At a meeting of Yale’s Trumbull Beer and Bike Society, one student declared he could beat another in a bicycle race all the way to Vassar. However, this valiant duel between two determined Trumbull residents quickly became a popular annual tradition in the early 1950s and a day on which the iconic style of the Seven Sisters and Ivy colleges revealed a sense of humor.

Each April, there was a Yale mass exodus, with around sixteen five-man teams pedaling the some 70 miles from New Haven to Poughkeepsie, eager to be reunited with their “waiting Vassar femmes.” The rules? First team to Vassar won, fancy dress optional but preferred, and, to make things just a little bit more interesting, at each change-over on the relay one team-member had to guzzle a quart of beer before the next man began cycling.

While Yale and Vassar had long since enjoyed an academic connection, the 1950s saw this relationship become even more important socially. Vassar’s resident Warden, Elizabeth Drouilhet, remembered that in the early 1950s, “Students felt that they were totally isolated from the opposite sex. There were any number of attempts to try to counteract our geographic location.” Namely, there was the introduction of Vassar-Yale mixers and dances, however neither school actually sanctioned the race. Drouilhet described the race as a way for restless students in the post-World War II era to prove “what absurdities one could get into.” While over at Yale, Dean Harold B. Whiteman simply reasoned that, for the men at least, “I think this type of exercise a great deal better than face slapping or eating live goldfish.”

For those men who completed the race (and by all accounts injuries, exhaustion, inebriation and even simply disorientation hampered many efforts), their costumes poked fun at both the typical look of the Yalie and aspects of Yale history.

Present were the madras and khaki Bermudas, socks, loafers and saddle shoes, but with comedic accessories: one team adopted college ties, moustaches and bowler hats and still managed to complete the race. Another team fashioned a “Yale News Press-Cycle” and, complete with comedy goggles, flat caps and raccoon coats, and pedaled their way into Poughkeepsie. The more athletic teams in ’52 (although only one team actually trained for the race) even created their own sports uniforms emblazoned with team names like “The Over SEX-ted” or “The Maidenform Five.” And in later years there were the “Papa Peacocks” and their supporters “The Sex-Tots.”

But the girls also enjoyed a good time, and while some wrapped themselves in polo coats due to the April chill, wearing Yale scarves and waving blue and white pennants, others adopted outrageous fancy dress that paid homage to Vassar’s history. One year two girls arrived as “Mr. and Mrs. Vassar Brew,” dressed in 19th-century costumes in a nod to both Vassar’s brewing roots and the Beer and Bike Society. Despite all the drunken fun of the day, Vassar’s ban on alcohol on campus meant that supporters and cyclists had to congregate just outside the main gate to celebrate. This led another duo to wear light dresses as “Wisdom and Purity,” reportedly to “uphold the [Vassar] seal by confiscating empty beer cans.”

Nonetheless, after the victors were crowned and the triumphant beers were drunk, traditional Vassar and Yale style was restored. A banquet and dance was always held, where students could rejoin their fiancés and dates, listen to acapella music from the Vassar Flora Doras and Yale Whiffenpoofs, and tend to any injuries. The styles showcased at the celebrations reaffirmed Yale and Vassar as two of the most important schools in setting collegiate fashion trends: The men wore their club jackets and Brooks Brothers shirts and ties, while Vassar students donned their own collegiate garb in the form of Fair Isle sweaters, Bermuda shorts, official Vassar College blazers, and plaid skirts.

The race got its most high profile coverage at the 1952 running, when LIFE magazine sent photographers to capture the chaotic scenes, but actually the race continued to run annually until 1954. Unfortunately the extravagances of the race, not to mention the dangers, led the college administrations to step in and cancel the event.

Yet for those few years the event captured a sense of collegiate fun and serves as an excellent lesson in iconic midcentury Ivy and Vassar style. — REBECCA C. TUITE

Rebecca C. Tuite is a writer and fashion historian based in London currently pursuing graduate studies at University of the Arts. Her research is focused on collegiate American fashion, including the construction of the Vassar Girl style as a key archetype of American fashion and womanhood in 1950s American media. She completed her undergraduate studies at both the University of Exeter and Vassar College.

All images are from the LIFE Magazine archives and are copyright Time Inc.

We scoured the archives at the Yale library and although cycling history was tough to find, it wasn't impossible. The team has a rich history dating back over a century. We've collected some of our favorite images of teams, riders, and events from our past.

For a time, the Trumbull Beer N' Bike Race was an annual mixer between Yale and Vassar centered around a race from New Haven to Poughkeepsie. Yale participants raced segments and chugged beer in relay fashion. LIFE Magazine chronicled the events in 1952 in the best way they know how - with beautiful black and white photos. There's plenty of drinking, cycling, and odd costumes, which leaves only one question to be answered: Why did we ever stop doing this?